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Updated: Jun 17, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Structure-reactivity relationships: reactions of a 5-substituted aziadamantane in a resorcin[4]arene-based cavitand
Gerald Wagner1, Wolfgang Knoll, Michael M Bobek
1Institute of Organic Chemistry, University of Vienna, Wahringer Strasse 38, A-1090 Vienna, Austria.
Abstract:
The complexation properties of two novel C5-substituted adamantanediazirines within the resorcin[4]arene-based cavitand 4 were investigated in DMSO-d(6), revealing that binding is up to 1.4 kcal/mol stronger for halogenated adamantanediazirines when compared with the unsubstituted species. The thermal behavior of 5-bromo-2-aziadamantane (3) was investigated by DSC analysis as the first representative of the adamantanediazirine family in the neat solid state, as well as encapsulated within the aromatic cavity of cavitand 4. In the solid phase, the reactions of photolytically or thermolytically generated 5-bromo-2-adamantanylidene (11) can be controlled by complexation within cavitand 4.
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